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2support the contention that the female pheromone is the dominant factor in malefemalesearching. Figure 1 shows both female and male California Red Scale.Current methods of controlling California Red Scale include both pesticidetreatment and biological control. 3,4 The most common pesticide treatment usesbroad spectrum organophosphate and carbamate insecticides. These sweepingpesticides have two main disadvantages. First, they kill natural predators ofCalifornia Red Scale and second, some California Red Scale have becomeresistant to all forms of pesticide. Another method of controlling California RedScale is biological control. This type of control is characterized by controlledrelease of natural predators to California Red Scale. The most important naturalpredator is the parasitic wasp, Aphytis melinus. In the San Joaquin Valley, atypical release rate of Aphytis is 100,000 parasites per acre per year. Thedisadvantages to this method of control are cost and time.Pheromone traps are used to trap male Red Scale in flight seeking toreproduce with the female Red Scale. 3 Important information is obtained by maleRed Scale pheromone trap counts including determination of when male flights areoccurring, which citrus orchards have high levels of Red Scale infestation, andhow to time insecticide applications. The pheromone trap is charged with asample of synthetic female California Red Scale pheromone which lures the maleto the trap. The pheromone trap, therefore, serves two purposes: (a) it providesinformation on Red Scale population and (b) the control of Red Scale populationby the prevention of reproduction. Figure 2 shows a pheromone trap in the field.In 1977, the active components of the California Red Scale female sexpheromone were discovered by collaborative effort between the United StatesDepartment of Agriculture and Zoecon Corporation of Palo Alto, California. 5These components were 3-methyl-6-isopropenyl-9-decen-1-yl acetate and (Z)-3-
3a. Adult Female California Red Scaleb. Adult Male California Red ScaleFigure 1. California Red Scale (Aonidiella aurantii)
Page 1: ABSTRACTASYMMETRIC SYNTHESIS OF 6,7
Page 4 and 5: NOTE:THIS PAGE IS OPTIONAL, AND REQ
Page 6 and 7: APPROVEDFor the Department of Chemi
Page 8 and 9: ACKNOWLEDGMENTSI would like to than
Page 10 and 11: FigureLIST OF FIGURESPage1. Califor
Page 12 and 13: 37.38.39.ix13 C NMR Spectrum of (3S
Page 16 and 17: Figure 2. California Red Scale pher
Page 18 and 19: 6creation of the chiral center at C
Page 20 and 21: 8During the early 1990s Professor E
Page 22 and 23: 10across the top of the molecule, a
Page 24 and 25: 12molecule and also shows that the
Page 26 and 27: 14Figure 10. (R,R) Jacobsen’s cat
Page 28 and 29: 16stereoselectivity. With tri-subst
Page 30 and 31: 18physical properties (except optic
Page 32 and 33: 20Calo in 1990 published a method o
Page 34 and 35: 22halide into an excess of magnesiu
Page 36 and 37: RESULTS AND DISCUSSIONSynthesis of
Page 38 and 39: Figure 18. 1 H NMR spectrum of (3S)
Page 40 and 41: Figure 20. GC/MS trace of (3S) citr
Page 42 and 43: Figure 22. 1 H NMR spectrum of (3S,
Page 44 and 45: 32IR spectroscopy .Separation of Ep
Page 46 and 47: Figure 25. GC/MS trace of (3S,6RS)-
Page 52 and 53: 40due to the starting material (3S)
Page 54 and 55: 42Figure 33. 1 H NMR spectrum of (3
Page 56 and 57: Figure 36. 13 C NMR spectrum of (3S
Page 58 and 59: 46Figure 37. 13 C NMR Spectrum of (
Page 60 and 61: 48major peak by GC/MS (Figure 40).
Page 62 and 63: Figure 42. Results of GC/MS library
Page 64 and 65:
52GC/MS trace showed that only inte
Page 66 and 67:
EXPERIMENTALAll 1 H Nuclear Magneti
Page 68 and 69:
56Synthesis of (3S,6RS)-6,7-Epoxyci
Page 70 and 71:
58catalyst in the product. Another
Page 72 and 73:
60was observed and no temperature c
Page 74 and 75:
REFERENCES1. Bodenheimer, F.S. Citr
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